No. Not at all.
While I would love to see Ash win a league, it would effectively put an end to his story for the most part. (There are ways he can continue but nothing that would be worth dragging him along even MORE) Him actually succeeding in the anime would require the writers to be willing to take a huge risk by creating another main character and replacing Ash with him/her after Ash wins. Sadly I don't think the writers will ever be willing to do that. The steady income of cash the anime gives now is more appealing to them then trying to actually do something new and exciting for a change at the risk of upsetting the established flow. Shame really, since there are so many interesting ideas they could make use of if they were willing to try.